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Amine Protection/α-Activation with the tert-Butoxythiocarbonyl Group: Application to Azetidine Lithiation–Electrophilic Substitution

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posted on 2015-12-17, 06:59 authored by David M. Hodgson, Claire L. Mortimer, Jeffrey M. McKenna
tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N′,N′-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding N-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol.

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